How To Dress For A Date

How To Dress For A Date
Valentine’s Style
You’ve managed to secure a reservation at that superb restaurant, you’ve placed your order at their favourite florist and, after plenty of deliberation, you’ve settled on the perfect gift that shows just how much you care.
Now what the hell are you going to wear?
It’s surprisingly easy to leave this most important aspect of a Valentine’s date to the last minute, but it’s worth bearing in mind that failing to dress for the occasion after you’ve invested in everything from artisan chocolates to a surprise weekend getaway is about the same as pairing your knackered dirty Converse with your finest tuxedo – you’re simply not doing yourself justice.
But that’s not to say that you should be wearing your Sunday finest to your afternoon brunch date. It’s all about making sure that you dress both stylishly and appropriately for whatever you’ve got planned.
With this in mind, we’re giving you a rundown on what to wear to four common Valentine’s date scenarios.
The Dinner Date
Good choice; how can you go wrong with three courses of masterfully prepared aphrodisiacs accompanied by a few glasses of fine wine? Taking your date to dinner on Valentine’s Day is pretty much fail-safe – and if you’ve jumped the hurdles involved in securing a reservation, then you’ll want to match that same effort when it comes to what you wear.
It’s hard to beat a sharp suit in this instance. Given that you’ve opted for arguably the most traditional type of Valentine’s date, keep your look similarly classic by opting for a two-button, notch lapel style in light grey, charcoal, navy or black.
Remember: your aim here is to appear well-dressed and attractive, not upstage your date and make them feel uncomfortable. With this in mind, round out the look with a simple white button-down shirt or roll neck in a complementary colour, a pair of classic black Derbies/Oxfords and a neatly folded pocket square that sits firmly on the subtle, rather than showy, side of the spectrum.
If a suit is a little too much for you or the restaurant in question, then revert to a foolproof chino and blazer combo. Try a pair of slim- to straight-fit chinos in beige with a navy tweed blazer, blue Oxford shirt and pair of brown brogues or loafers. If you want to add a little formality to mark the occasion, consider introducing a plain coloured knitted tie.
Example Suit Looks
Men's Date Outfit Inspiration Lookbook - Suits and Tailoring - The Fancy Restaurant Date
Example Separates Looks
Men's Date Outfit Inspiration Lookbook - Tailored Separates - The Fancy Restaurant Date
Key Pieces
  • AUTOGRAPH GREY SLIM FIT SUITAutograph Grey Slim Fit Suit
  • J. CREW LUDLOW SUIT JACKET IN ITALIAN COTTON PIQUEJ. Crew Ludlow Suit Jacket In Italian Cotton Pique
  • REISS SILVER MODERN FIT SUIT NAVYReiss Silver Modern Fit Suit Navy
  • ASOS SLIM FIT BLAZER IN TWEEDAsos Slim Fit Blazer In Tweed
  • M&S COLLECTION PURE COTTON TAILORED FIT TWILL JACKETM&s Collection Pure Cotton Tailored Fit Twill Jacket
  • REISS MULLER B FLECK WEAVE BLAZER NAVYReiss Muller B Fleck Weave Blazer Navy
  • HE BY MANGO STRAIGHT-FIT COTTON CHINOSHe By Mango Straight-fit Cotton Chinos
  • REISS TULLUM HEAVYWEIGHT TWILL CHINOS GREYReiss Tullum Heavyweight Twill Chinos Grey
  • J.CREW 484 SLIM-FIT WASHED-COTTON TROUSERSJ.crew 484 Slim-fit Washed-cotton Trousers
  • REISS ASCOT BUTTON-DOWN OXFORD SHIRT SKY BLUEReiss Ascot Button-down Oxford Shirt Sky Blue
  • SELECTED COTTON ROLL NECK JUMPERSelected Cotton Roll Neck Jumper
  • UNIQLO MEN EASY CARE BROADCLOTH LONG SLEEVE SHIRTUniqlo Men Easy Care Broadcloth Long Sleeve Shirt
  • TOPMAN HUDSON REYES BLACK LEATHER LOAFERSTopman Hudson Reyes Black Leather Loafers
  • REISS CERRONI HAND-FINISHED BROGUES MID BROWNReiss Cerroni Hand-finished Brogues Mid Brown
  • HE BY MANGO LEATHER BLUCHERHe By Mango Leather Blucher
The Cinema Date
We can’t give you advice on what to watch, but we’re more than happy to point you in the right direction when it comes to attire. A trip to the flicks may be a little more low-key than a dinner date, but that’s still no reason for you to slack on the style count.
You’ll want to aim for the smarter end of smart-casual for this one, just in case you end up going for drinks before or after. Start off with a solid pair of winter-weight fabric trousers such as beige moleskin chinos, indigo selvedge jeans, brown/burgundy cords or grey flannel trousers.
Build on your base with a plain cotton, plaid or chambray button-down shirt and a generously sized knit to ward off the chill – a chunky cable jumper or shawl neck cardigan would be ideal – then polish your look off with a pair of smart boots in brown/black.
We’re not promising anything but if this combination of textures doesn’t encourage your date to get tactile, then there’s little that will.
Lookbook Inspiration
Men's Date Outfit Inspiration Lookbook - The Cinema and Drinks Date
Key Pieces
  • SHORE LEAVE MELANGE OXFORD SHIRT IN GREYShore Leave Melange Oxford Shirt In Grey
  • HE BY MANGO SHAWL COLLAR COTTON CARDIGANHe By Mango Shawl Collar Cotton Cardigan
  • HE BY MANGO CHUNKY KNIT CARDIGANHe By Mango Chunky Knit Cardigan
  • FARAH VINTAGE TROUSERS IN GREY HERRINGBONEFarah Vintage Trousers In Grey Herringbone
  • TOPMAN LEVIS VINTAGE CLOTHING 501 SHRINK-TO-FIT SELVEDGE DENIM JEANSTopman Levis Vintage Clothing 501 Shrink-to-fit Selvedge Denim Jeans
  • TOPMAN BROWN TEXTURED SKINNY FIT SUIT TROUSERSTopman Brown Textured Skinny Fit Suit Trousers
  • J.CREW SLIM-FIT BUTTON DOWN-COLLAR CHECKED COTTON SHIRTJ.crew Slim-fit Button Down-collar Checked Cotton Shirt
  • ALEX MILL BUTTON-DOWN COLLAR DENIM SHIRTAlex Mill Button-down Collar Denim Shirt
  • REISS BUTLER SHAWL COLLAR CARDIGAN ECRUReiss Butler Shawl Collar Cardigan Ecru
  • AUSTIN REED NEUTRAL MOLESKIN TROUSERSAustin Reed Neutral Moleskin Trousers
  • CLUB MONACO CORDUROY TROUSERSClub Monaco Corduroy Trousers
  • LEVIS VINTAGE CLOTHING 501 SHRINK-TO-FIT SELVEDGE DENIM JEANSLevis Vintage Clothing 501 Shrink-to-fit Selvedge Denim Jeans
  • RIVER ISLAND BROWN SUEDE CHUKKA BOOTSRiver Island Brown Suede Chukka Boots
  • H BY HUDSON HOUGHTON BOOTS IN TANH By Hudson Houghton Boots In Tan
  • ASOS CHELSEA BOOTS IN SUEDEAsos Chelsea Boots In Suede
The Day Date
Whether it’s a day trip to a neighbouring town or city, a visit to your favourite museum or a scenic lakeside walk, this option is likely to see you moving in- and outdoors throughout the day, meaning savvy layering is paramount to looking and feeling your best.
Ensure you’re prepared for every kind of weather February can throw at you by teaming a lightweight jacket – think mac, trench, field, unlined parka, etc. – with a mid-weight piece of knitwear, classic crew neck tee and pair of dark indigo jeans or slim chinos.
When it comes to footwear, you’ll want to go for a style that’s both sturdy and comfortable – boots (whether a classic brogue silhouette or worker-inspired style) and leather trainers are your best options here.
If it’s chilly, don’t forget your cashmere scarf and leather gloves – both are luxurious yet understated and will give off a subtle sense of sophistication.
Lookbook Inspiration
Men's Date Outfit Inspiration Lookbook - The Relaxed Day Date
Key Pieces
  • ALLSAINTS MEAKAN CREW JUMPERAllsaints Meakan Crew Jumper
  • ASOS ROLL NECK JUMPER IN COTTONAsos Roll Neck Jumper In Cotton
  • POLO RALPH LAUREN PLAIN OXFORD SLIM FIT SHIRTPolo Ralph Lauren Plain Oxford Slim Fit Shirt
  • UNIQLO MEN EXTRA FINE COTTON BROADCLOTH CHECK LONG SLEEVE SHIRTUniqlo Men Extra Fine Cotton Broadcloth Check Long Sleeve Shirt
  • HE BY MANGO CABLE-KNIT COTTON SWEATERHe By Mango Cable-knit Cotton Sweater
  • HE BY MANGO WATER-REPELLENT NYLON TRENCH COATHe By Mango Water-repellent Nylon Trench Coat
  • RIVER ISLAND NAVY HOLLOWAY ROAD STRUCTURED COATRiver Island Navy Holloway Road Structured Coat
  • REISS STORM BELTED JACKET BLACKReiss Storm Belted Jacket Black
  • REISS TULLUM HEAVYWEIGHT TWILL CHINOS KHAKIReiss Tullum Heavyweight Twill Chinos Khaki
  • POLO RALPH LAUREN SLIM-FIT COTTON-CHAMBRAY SHIRTPolo Ralph Lauren Slim-fit Cotton-chambray Shirt
  • LEVIS VINTAGE CLOTHING 1950S MARLED COTTON SWEATSHIRTLevis Vintage Clothing 1950s Marled Cotton Sweatshirt
  • NN.07 JAMES SLIM-FIT RINSED DENIM JEANSNn.07 James Slim-fit Rinsed Denim Jeans
  • AUSTIN REED CLASSIC BROWN LEATHER GLOVESAustin Reed Classic Brown Leather Gloves
  • COLLEZIONE PURE CASHMERE SCARFCollezione Pure Cashmere Scarf
  • UNIQLO MEN SLIM FIT CHINO FLAT FRONT TROUSERSUniqlo Men Slim Fit Chino Flat Front Trousers
The Home Date
Probably the most intimate option, just because you won’t be leaving your home doesn’t mean your trusty jeans and hoody combination makes the cut. You’ll definitely need to appear put-together, but it’s advisable to stop short of looking like you’ve tried too hard.
Keep your outfit relaxed but presentable. Try a pair of straight-leg jeans or chinos with a shirt and lightweight v- or crew neck jumper, or a knit polo shirt with a pair of nattily cut trousers.
While footwear won’t be at the forefront of your mind, we’d suggest you swap the pool slides or slippers for a pair of tasselled loafers, minimal trainers or desert boots. If you’re a ‘no shoes inside the house’ type of guy, please make sure your socks haven’t got holes in and that theycomplement your ensemble.
Lookbook Inspiration
Men's Date Outfit Inspiration Lookbook - The Home Date
Key Pieces
  • HE BY MANGO SHAWL-COLLAR TEXTURED CARDIGANHe By Mango Shawl-collar Textured Cardigan
  • FARAH OXFORD SHIRT IN WHITEFarah Oxford Shirt In White
  • ASOS LAMBSWOOL RICH CARDIGANAsos Lambswool Rich Cardigan
  • HE BY MANGO STRAIGHT-FIT COTTON CHINOSHe By Mango Straight-fit Cotton Chinos
  • HE BY MANGO SLIM-FIT DARK JAN JEANSHe By Mango Slim-fit Dark Jan Jeans
  • REISS SULTAN CONTRAST TEXTURED JUMPER BLUE/BLACKReiss Sultan Contrast Textured Jumper Blue/black
  • JOHN SMEDLEY TEXTURED-KNIT COTTON SHAWL-COTTON CARDIGANJohn Smedley Textured-knit Cotton Shawl-cotton Cardigan
  • J.CREW V-NECK CASHMERE SWEATERJ.crew V-neck Cashmere Sweater
  • NUDIE JEANS TIGHT LONG JOHN SLIM-FIT ORGANIC DRY-DENIM JEANSNudie Jeans Tight Long John Slim-fit Organic Dry-denim Jeans
  • REISS MARSHALL POCKET DETAIL T-SHIRT CHARCOALReiss Marshall Pocket Detail T-shirt Charcoal
  • REISS SPHINX WOOL POLO SHIRT BRIGHT BLUEReiss Sphinx Wool Polo Shirt Bright Blue
  • REISS QUEENS CONTRAST WEAVE JUMPER BERRYReiss Queens Contrast Weave Jumper Berry
  • ADIDAS STAN SMITH VULC TRAINERS IN WHITEAdidas Stan Smith Vulc Trainers In White
  • RIVER ISLAND SMART SHOESRiver Island Smart Shoes
  • HE BY MANGO SUEDE DESERT BOOTSHe By Mango Suede Desert Boots
The All-Important Details
Finally, don’t go to the effort of crafting the perfect date – and the outfit to go with it – without making sure your grooming is up to scratch.
Drop by your barber beforehand for a fresh cut so your hair is looking on point and don’t forget to set aside some time for a clean shave or trim – a little manscaping wouldn’t go amiss either.
We’ll say this once and once only: when it comes to fragrance, be sparing with your chosen scent. While a few modest dashes of cologne are crucial for impressing your date, too liberal an application will only serve to suffocate them.
Final Word
With four of the major types of dates to go on checked off, you’re covered for most romantic bases this Valentine’s Day.
So, what will you be wearing? Where are you taking your significant other? Any essential tips to bear in mind when planning the charm offensive?
Let us know in the comments section.